JP2000198821A - Vinyl chloride-vinyl acetate-based copolymer and composition - Google Patents
Vinyl chloride-vinyl acetate-based copolymer and compositionInfo
- Publication number
- JP2000198821A JP2000198821A JP117899A JP117899A JP2000198821A JP 2000198821 A JP2000198821 A JP 2000198821A JP 117899 A JP117899 A JP 117899A JP 117899 A JP117899 A JP 117899A JP 2000198821 A JP2000198821 A JP 2000198821A
- Authority
- JP
- Japan
- Prior art keywords
- vinyl
- vinyl acetate
- vinyl chloride
- acetate copolymer
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、不飽和カルボン酸
および／または酸無水物成分（Ａ）と炭素数４以上の長
鎖脂肪酸ビニルエステル成分（Ｂ）のモル比（Ａ／Ｂ）
が１．０×１０-4から１．６×１０2の範囲で含有して
なる塩化ビニル−酢酸ビニル系共重合体およびその組成
物に関し、本発明の塩化ビニル−酢酸ビニル系共重合体
は、優れた密着性および高度な耐候性を有し、かつ広範
な有機系溶媒選択性を有するものである。The present invention relates to an unsaturated carboxylic acid and / or acid anhydride component (A) and a long-chain fatty acid vinyl ester component having 4 or more carbon atoms (B) (A / B).
Is contained in the range of 1.0 × 10 −4 to 1.6 × 10 2 , and a composition thereof, and the vinyl chloride-vinyl acetate copolymer of the present invention is: It has excellent adhesion and high weather resistance, and has a wide range of organic solvent selectivity.
【０００２】[0002]
【従来の技術】塩化ビニル−酢酸ビニル系共重合体はそ
の密着性、柔軟性、難燃性などの優れた性能から塗料、
接着剤、インクなどに使用される樹脂組成物として広く
使用されている。また、これら塩化ビニル−酢酸ビニル
系共重合体はアルコール類、エステル類、ケトン類、芳
香族炭化水素類、水等の溶媒又は分散媒と共に塩化ビニ
ル−酢酸ビニル系共重合体組成物として使用されてい
る。2. Description of the Related Art Vinyl chloride-vinyl acetate copolymers are used for coatings,
It is widely used as a resin composition used for adhesives, inks, and the like. These vinyl chloride-vinyl acetate copolymers are used as a vinyl chloride-vinyl acetate copolymer composition together with a solvent or a dispersion medium such as alcohols, esters, ketones, aromatic hydrocarbons and water. ing.
【０００３】塩化ビニル−酢酸ビニル系共重合体を有機
系溶媒に溶解した塩化ビニル−酢酸ビニル系共重合体組
成物を塗料として用いる場合、密着性および耐候性の他
に、塗料を希釈する際に有機系溶媒選択性が広いこと、
つまり、広範な有機系溶媒選択性を有することが塩化ビ
ニル−酢酸ビニル系共重合体に要求されている。When a vinyl chloride-vinyl acetate copolymer composition obtained by dissolving a vinyl chloride-vinyl acetate copolymer in an organic solvent is used as a paint, not only adhesiveness and weather resistance, but also when the paint is diluted. Wide organic solvent selectivity,
That is, a vinyl chloride-vinyl acetate copolymer is required to have a wide range of organic solvent selectivity.
【０００４】[0004]
【発明が解決しようとする課題】本発明は従来の塩化ビ
ニル−酢酸ビニル系共重合体を改善し、優れた密着性お
よび高度な耐候性を有し、かつ広範な有機系溶媒選択性
を有する塩化ビニル−酢酸ビニル系共重合体、およびそ
けを含有してなる塩化ビニル−酢酸ビニル系共重合体組
成物を提供するものである。SUMMARY OF THE INVENTION The present invention is an improvement over conventional vinyl chloride-vinyl acetate copolymers, has excellent adhesion and high weather resistance, and has a wide range of organic solvent selectivity. A vinyl chloride-vinyl acetate copolymer and a vinyl chloride-vinyl acetate copolymer composition containing the same.
【０００５】[0005]
【課題を解決するための手段】すなわち本発明は塩化ビ
ニル−酢酸ビニル系共重合体組成物中に、不飽和カルボ
ン酸および／または酸無水物と炭素数４以上の長鎖脂肪
酸ビニルエステルの成分を特定のモル比の範囲内で共重
合することによって、優れた密着性および高度な耐候性
を有し、かつ広範な有機系溶媒選択性を有する塩化ビニ
ル−酢酸ビニル系共重合体を得るものであり、当該共重
合体はその有機系溶媒選択性が広いので例えば塗料に好
適に使用される塩化ビニル−酢酸ビニル系共重合体組成
物を提供する。That is, the present invention relates to a vinyl chloride-vinyl acetate copolymer composition comprising a component of an unsaturated carboxylic acid and / or acid anhydride and a long-chain fatty acid vinyl ester having 4 or more carbon atoms. Is obtained in a specific molar ratio range to obtain a vinyl chloride-vinyl acetate copolymer having excellent adhesion and high weather resistance, and having a wide range of organic solvent selectivity. Since the copolymer has a wide selectivity for organic solvents, it provides a vinyl chloride-vinyl acetate copolymer composition suitably used for, for example, a coating material.
【０００６】[0006]
【発明の実施の形態】本発明の塩化ビニル−酢酸ビニル
系共重合体は不飽和カルボン酸および／または酸無水物
の成分（Ａ）と炭素数４以上の長鎖脂肪酸ビニルエステ
ル成分（Ｂ）を共重合してなるものである。DETAILED DESCRIPTION OF THE INVENTION The vinyl chloride-vinyl acetate copolymer of the present invention comprises an unsaturated carboxylic acid and / or acid anhydride component (A) and a long-chain fatty acid vinyl ester component having 4 or more carbon atoms (B). Are copolymerized.
【０００７】ここで、不飽和カルボン酸としては、例え
ばフマル酸、マレイン酸、イタコン酸、シトラコン酸、
ビニル安息香酸がある。また、酸無水物としては、例え
ば無水マレイン酸、無水イタコン酸、無水シトラコン酸
などのカルボン酸を有するビニル単量体がある。不飽和
カルボン酸と酸無水物は単独で共重合しても、あるいは
両成分を共重合してもよい。The unsaturated carboxylic acids include, for example, fumaric acid, maleic acid, itaconic acid, citraconic acid,
There is vinylbenzoic acid. Examples of the acid anhydride include vinyl monomers having a carboxylic acid such as maleic anhydride, itaconic anhydride and citraconic anhydride. The unsaturated carboxylic acid and the acid anhydride may be copolymerized alone or both components may be copolymerized.
【０００８】炭素数４以上の長鎖脂肪酸ビニルエステル
としては、例えばネオデカン酸ビニルエステル、ラウリ
ル酸ビニルエステル、ステアリン酸ビニルエステルなど
がある。Examples of the vinyl ester of a long-chain fatty acid having 4 or more carbon atoms include vinyl neodecanoate, vinyl laurate and vinyl stearate.
【０００９】塩化ビニル−酢酸ビニル系共重合体中に共
重合される不飽和カルボン酸および／または酸無水物の
成分（Ａ）と炭素数４以上の長鎖脂肪酸ビニルエステル
の成分（Ｂ）のモル比（Ａ／Ｂ）は１．０×１０-4から
１．６×１０2である。モル比がその範囲を外れると密
着性等の物性が低下し好ましくない。The component (A) of the unsaturated carboxylic acid and / or acid anhydride copolymerized in the vinyl chloride-vinyl acetate copolymer and the component (B) of the vinyl ester of a long-chain fatty acid having 4 or more carbon atoms are used. The molar ratio (A / B) is from 1.0 × 10 −4 to 1.6 × 10 2 . If the molar ratio is out of the range, physical properties such as adhesion are undesirably reduced.
【００１０】ＡおよびＢの成分の合計は共重合体中に１
から５０重量％であることが好ましい。１重量％より小
さいと密着性が低下する傾向となる。５０重量％を超え
ると特に不飽和カルボン酸および／又は酸無水物が多い
場合耐水性が低下する傾向となる。The total of components A and B is 1 in the copolymer.
To 50% by weight. If it is less than 1% by weight, the adhesiveness tends to decrease. If it exceeds 50% by weight, the water resistance tends to decrease particularly when the content of unsaturated carboxylic acid and / or acid anhydride is large.
【００１１】不飽和カルボン酸および／または酸無水物
の成分と炭素数４以上の長鎖脂肪酸ビニルエステルの成
分のモル比、含有量は塩化ビニル−酢酸ビニル系共重合
体を製造する際にその仕込み量より算出することができ
る。或いは、塩化ビニル−酢酸ビニル系共重合体をＮＭ
Ｒ、塩素含量の測定等により測定することによっても求
めることが出来る。この方法は塩化ビニル−酢酸ビニル
系共重合体を製造する際に単量体が残存する状態で重合
を停止するような方法を用いた場合に好適に使用するこ
とができる。The molar ratio and content of the component of the unsaturated carboxylic acid and / or acid anhydride and the component of the long-chain fatty acid vinyl ester having 4 or more carbon atoms are determined when producing a vinyl chloride-vinyl acetate copolymer. It can be calculated from the charged amount. Alternatively, a vinyl chloride-vinyl acetate copolymer is NM
It can also be determined by measuring R and chlorine contents. This method can be suitably used when a method is used in which the polymerization is stopped in a state where the monomer remains when a vinyl chloride-vinyl acetate copolymer is produced.
【００１２】本発明の塩化ビニル−酢酸ビニル系共重合
体は各種有機溶剤に溶解させて塩化ビニル−酢酸ビニル
系共重合体組成物とすることができ、この物に更に顔
料、染料、着色剤、充填剤、酸化防止剤、紫外線吸収剤
等を添加したものは塗料として好適に使用することがで
きる。The vinyl chloride-vinyl acetate copolymer of the present invention can be dissolved in various organic solvents to form a vinyl chloride-vinyl acetate copolymer composition. Those containing a filler, an antioxidant, an ultraviolet absorber and the like can be suitably used as a paint.
【００１３】[0013]
【実施例】以下、本発明を実施例に基づいて説明する。
なお、以下の各例中の部は重量部を表す。DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below based on embodiments.
The parts in the following examples represent parts by weight.
【００１４】（実施例１）撹拌機、導入管を付けた５Ｌ
のＳＵＳ製オートクレーブに酢酸ビニル２５部、作業中
作業中不飽和カルボン酸成分としてマレイン酸０．８
部、炭素数４以上の長鎖脂肪酸ビニルエステル成分とし
てネオデカン酸ビニルエステル（商品名ベオバ１０、シ
ェルジャパン社製）５部、酢酸エチル３４．５部、トル
エン２７．５部およびラジカル発生剤パーブチルＯ（日
本油脂社製）０．５部を仕込み、密封して窒素加圧した
後、減圧して塩化ビニル７０部を仕込んだ。これを６０
℃の水浴中で撹拌しながら４０時間保温して、重合反応
を行った。得られた塩化ビニル−酢酸ビニル系共重合体
にトルエン５０部を加え、固形分４５％の塩化ビニル−
酢酸ビニル系共重合体組成物を得た。塩化ビニル−酢酸
ビニル系共重合体中のマレイン酸とネオデカン酸ビニル
エステルのモル比はその仕込み量より（０．８／１１
６．０７）／（５／１９９）となりその値は０．２７で
あった。また両成分はその仕込み量より５．８重量％で
あった。Example 1 5 L with stirrer and inlet tube
In a SUS autoclave, 25 parts of vinyl acetate was used.
Part, 5 parts of neodecanoic acid vinyl ester (trade name: Beova 10, manufactured by Shell Japan Co., Ltd.) as a long-chain fatty acid vinyl ester component having 4 or more carbon atoms, 34.5 parts of ethyl acetate, 27.5 parts of toluene, and a radical generator perbutyl O 0.5 part (manufactured by Nippon Oil & Fats Co., Ltd.) was charged, sealed, pressurized with nitrogen, and then depressurized to charge 70 parts of vinyl chloride. This is 60
The polymerization reaction was carried out by keeping the temperature for 40 hours while stirring in a water bath at ℃. To the obtained vinyl chloride-vinyl acetate copolymer was added 50 parts of toluene, and a vinyl chloride having a solid content of 45% was added.
A vinyl acetate copolymer composition was obtained. The molar ratio of maleic acid and vinyl neodecanoate in the vinyl chloride-vinyl acetate copolymer is determined by the charge amount (0.8 / 11).
6.07) / (5/199), and the value was 0.27. The content of both components was 5.8% by weight based on the charged amount.
【００１５】（比較例１）実施例１と同様な装置に酢酸
ビニル３０部、マレイン酸０．８部、酢酸エチル３４．
５部、トルエン２７．５部およびラジカル発生剤パーブ
チルＯ（日本油脂社製）０．５部を仕込み、密封して窒
素加圧した後、減圧して塩化ビニル７０部を仕込んだ。
これを６０℃の水浴中で撹拌しながら４０時間保温し
て、重合反応を行った。重合終了後トルエン５０部を加
え、固形分４５％の塩化ビニル−酢酸ビニル系共重合体
組成物を得た。Comparative Example 1 In a device similar to that of Example 1, 30 parts of vinyl acetate, 0.8 part of maleic acid and 34 parts of ethyl acetate were used.
5 parts, 27.5 parts of toluene and 0.5 parts of a radical generator perbutyl O (manufactured by NOF CORPORATION) were charged, sealed and pressurized with nitrogen, and then pressure-reduced, and 70 parts of vinyl chloride were charged.
This was kept warm for 40 hours while stirring in a water bath at 60 ° C. to carry out a polymerization reaction. After the completion of the polymerization, 50 parts of toluene was added to obtain a vinyl chloride-vinyl acetate copolymer composition having a solid content of 45%.
【００１６】（比較例２）実施例１と同様な装置に酢酸
ビニル２５部、ネオデカン酸ビニルエステル（商品名ベ
オバ１０、シェルジャパン社製）５部、酢酸エチル３
４．５部、トルエン２７．５部およびラジカル発生剤パ
ーブチルＯ（日本油脂社製）０．５部を仕込み、密封し
て窒素加圧した後、減圧して塩化ビニル７０部を仕込ん
だ。これを６０℃の水浴中で撹拌しながら４０時間保温
して、重合反応を行った。重合終了後トルエン５０部を
加え、固形分４５％の塩化ビニル−酢酸ビニル系共重合
体組成物を得た。(Comparative Example 2) In the same apparatus as in Example 1, 25 parts of vinyl acetate, 5 parts of vinyl neodecanoate (trade name: Beova 10, manufactured by Shell Japan), and 3 parts of ethyl acetate
4.5 parts, 27.5 parts of toluene and 0.5 part of a radical generator perbutyl O (manufactured by NOF CORPORATION) were charged, sealed and pressurized with nitrogen, and then pressure-reduced, and 70 parts of vinyl chloride were charged. This was kept warm for 40 hours while stirring in a water bath at 60 ° C. to carry out a polymerization reaction. After the completion of the polymerization, 50 parts of toluene was added to obtain a vinyl chloride-vinyl acetate copolymer composition having a solid content of 45%.
【００１７】（塗料の作成）実施例１、比較例１、２で
得られた塩化ビニル−酢酸ビニル系共重合体組成物１６
０ｇに酸化チタン７０ｇ、トルエン２５ｇ及び１．５ｍ
ｍのガラスビーズ３００ｇを５００ｍｌのポリエチ瓶に
秤量し、ペイントシェーカーで３時間震盪して酸化チタ
ンを分散させた後、ガラスビーズを濾過して除き、塗料
を得た。(Preparation of paint) The vinyl chloride-vinyl acetate copolymer composition 16 obtained in Example 1 and Comparative Examples 1 and 2
70 g of titanium oxide, 25 g of toluene and 1.5 m in 0 g
300 g of m glass beads were weighed into a 500 ml polyethylene bottle, shaken with a paint shaker for 3 hours to disperse the titanium oxide, and then the glass beads were removed by filtration to obtain a paint.
【００１８】（耐候性の評価）試験片として、ステンレ
スのプレート７０ｍｍ×１５０ｍｍに上記塗料を膜厚が
６０μｍになるようにスプレー塗装し、室温で１６８時
間乾燥したものを用いた。(Evaluation of Weather Resistance) As a test piece, a stainless steel plate of 70 mm × 150 mm was spray-coated so that the film thickness became 60 μm and dried at room temperature for 168 hours.
【００１９】試験片のサンシャインカーボンアーク灯式
耐候性試験は、ＪＩＳ Ｋ ５４００の促進耐候性の運
転条件に準じ、初期光沢に対する光沢保持率を測定し
た。In the sunshine carbon arc lamp type weather resistance test of the test piece, a gloss retention rate with respect to the initial gloss was measured according to the operating conditions of accelerated weather resistance according to JIS K5400.
【００２０】（密着性の評価）試験片として、ケイ酸カ
ルシウム板５０ｍｍ×１００ｍｍに乾燥後の塗布量が９
０ｇ／ｍ2となるように刷毛塗りし、室温で１６時間乾
燥したものを用いた。(Evaluation of Adhesion) As a test piece, a calcium silicate plate having a coating amount of 9 mm after drying was 50 mm × 100 mm.
A brush was applied so as to be 0 g / m 2 and dried at room temperature for 16 hours.
【００２１】試験片の密着性試験は、試験片をカッター
ナイフで３ｍｍ間隔で碁盤目状に６×７目を切り、セロ
ハン粘着テープを圧着した後、引き剥がして塗膜の残存
状態を見た。 ○：塗膜が剥離しない ×：塗膜が剥離したIn the adhesion test of the test piece, the test piece was cut in a grid pattern at intervals of 3 mm with a cutter knife in a 6 × 7 pattern, a cellophane adhesive tape was pressed, and then peeled off to check the remaining state of the coating film. . ○: The coating film did not peel off ×: The coating film peeled
【００２２】（有機溶媒選択性の評価：キシレン希釈
率）実施例１，比較例１、２で得られた塩化ビニル−酢
酸ビニル系共重合体組成物３０ｇを２００ｍｌビーカー
に入れ、スターラーによって撹拌しながらキシレンを６
ｍｌ／分の速度で滴下し、白濁するまでのキシレン滴下
量を測定した。(Evaluation of Organic Solvent Selectivity: Xylene Dilution Ratio) 30 g of the vinyl chloride-vinyl acetate copolymer composition obtained in Example 1 and Comparative Examples 1 and 2 was placed in a 200 ml beaker and stirred with a stirrer. 6 xylenes
The solution was dropped at a rate of ml / min, and the amount of xylene dropped until the solution became cloudy was measured.
【００２３】キシレン希釈率は、下記の式１に従い求め
た。The xylene dilution ratio was determined according to the following equation 1.
【００２４】[0024]
【式１】 (Equation 1)
【００２５】本願発明の実施例１は表１において良好な
物性を示したが、不飽和カルボン酸および／または酸無
水物成分または炭素数４以上の長鎖脂肪酸ビニルエステ
ル成分のどちらかの成分を欠く比較例は実施例１に比較
し耐候性、密着性、キシレン希釈率で劣ることが明らか
である。Example 1 of the present invention showed good physical properties in Table 1, but showed that either an unsaturated carboxylic acid and / or acid anhydride component or a long-chain fatty acid vinyl ester component having 4 or more carbon atoms was used. It is apparent that the comparative example lacking in comparison with Example 1 was inferior in the weather resistance, the adhesion, and the xylene dilution ratio.
【００２６】[0026]
【表１】 [Table 1]
【００２７】[0027]
【発明の効果】不飽和カルボン酸および／または酸無水
物成分（Ａ）と炭素数４以上の長鎖脂肪酸ビニルエステ
ル成分（Ｂ）をモル比（Ａ／Ｂ）が１．０×１０-4から
１．６×１０2の範囲で含有してなる塩化ビニル−酢酸
ビニル系共重合体は耐候性、密着性、キシレン希釈率等
の物性において優れその組成物は塗料に好適に使用され
る。According to the present invention, the molar ratio (A / B) of the unsaturated carboxylic acid and / or acid anhydride component (A) and the long-chain fatty acid vinyl ester component (B) having 4 or more carbon atoms (A / B) is 1.0 × 10 −4. The vinyl chloride-vinyl acetate copolymer contained in the range of from 1.5 to 1.6 × 10 2 is excellent in physical properties such as weather resistance, adhesion and xylene dilution ratio, and the composition is suitably used for coatings.
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Claims (3)
成分（Ａ）と炭素数４以上の長鎖脂肪酸ビニルエステル
成分（Ｂ）をモル比（Ａ／Ｂ）が１．０×１０-4から
１．６×１０2の範囲で含有してなる塩化ビニル−酢酸
ビニル系共重合体。An unsaturated carboxylic acid and / or acid anhydride component (A) and a long-chain fatty acid vinyl ester component (B) having 4 or more carbon atoms in a molar ratio (A / B) of 1.0 × 10 -4. To a vinyl chloride-vinyl acetate copolymer contained in the range of from 1.5 to 1.6 × 10 2 .
から５０重量％である請求項１記載の塩化ビニル−酢酸
ビニル系共重合体。2. The total of components A and B is 1 in the copolymer.
The vinyl chloride-vinyl acetate copolymer according to claim 1, wherein the amount of the copolymer is from 2 to 50% by weight.
ビニル系共重合体を含有してなる塩化ビニル−酢酸ビニ
ル系共重合体組成物。3. A vinyl chloride-vinyl acetate copolymer composition comprising the vinyl chloride-vinyl acetate copolymer according to claim 1 or 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP117899A JP2000198821A (en) | 1999-01-06 | 1999-01-06 | Vinyl chloride-vinyl acetate-based copolymer and composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP117899A JP2000198821A (en) | 1999-01-06 | 1999-01-06 | Vinyl chloride-vinyl acetate-based copolymer and composition |
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| Publication Number | Publication Date |
|---|---|
| JP2000198821A true JP2000198821A (en) | 2000-07-18 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP117899A Pending JP2000198821A (en) | 1999-01-06 | 1999-01-06 | Vinyl chloride-vinyl acetate-based copolymer and composition |
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| JP (1) | JP2000198821A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019029787A1 (en) * | 2017-08-07 | 2019-02-14 | Wacker Chemie Ag | Copolymers of vinyl chloride, vinyl acetate and long-chain vinyl esters |
| JP2019522701A (en) * | 2016-06-10 | 2019-08-15 | ピーピージー コーティングス ヨーロッパ ベーヴェー | Solvent-based binder for thermally expandable coatings |
-
1999
- 1999-01-06 JP JP117899A patent/JP2000198821A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019522701A (en) * | 2016-06-10 | 2019-08-15 | ピーピージー コーティングス ヨーロッパ ベーヴェー | Solvent-based binder for thermally expandable coatings |
| EP3469011B1 (en) * | 2016-06-10 | 2021-01-27 | PPG Coatings Europe B.V. | Solventborne binder for an intumescent coating |
| WO2019029787A1 (en) * | 2017-08-07 | 2019-02-14 | Wacker Chemie Ag | Copolymers of vinyl chloride, vinyl acetate and long-chain vinyl esters |
| JP2020530059A (en) * | 2017-08-07 | 2020-10-15 | ワッカー ケミー アクチエンゲゼルシャフトＷａｃｋｅｒ Ｃｈｅｍｉｅ ＡＧ | Copolymers of vinyl chloride, vinyl acetate and long chain vinyl esters |
| JP7262442B2 (en) | 2017-08-07 | 2023-04-21 | ワッカー ケミー アクチエンゲゼルシャフト | Copolymers of vinyl chloride, vinyl acetate and long-chain vinyl esters |
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